A new, enantioselective synthesis of (+)-isolaurepan

Pazos, Gonzalo; Pérez, Manuel; Gándara, Zoila; Gómez, Generosa; Fall, Yagamare

doi:10.1016/j.tetlet.2009.07.041

Cited by 23 publications

(14 citation statements)

References 47 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…As part of our ongoing program focusing on the use of readily available chiral substrate tri-Oacetyl-D-glucal (5) for the synthesis of natural products, [21][22][23][24][25] we wish now to report the synthesis of diospongin A, ent-diospongin A and C-5 epimer of diospongin B, using this compound. Our retrosynthetic basis is outlined in Scheme 1.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of diospongin A, ent-diospongin A and C-5 epimer of diospongin B from tri-O-acetyl-D-glucal

Zúñiga¹,

Pérez²,

Gándara³

et al. 2015

Arkivoc

Self Cite

View full text Add to dashboard Cite

show abstract

Section: Resultsmentioning

confidence: 99%

Synthesis of diospongin A, ent-diospongin A and C-5 epimer of diospongin B from tri-O-acetyl-D-glucal

Zúñiga¹,

Pérez²,

Gándara³

et al. 2015

Arkivoc

Self Cite

View full text Add to dashboard Cite

show abstract

“…More recently, the Ghosh group provided an alternative synthesis from the triacetyl ᴅ-glucal 60 ( Scheme 8 ) [ 31 ]. The exhaustive hydrolysis and selective protection as the 4,6- O -di- tert -butylsilylene derivative 61 [ 32 ] was followed by a 3- O -vinylation. A thermal 3,3-sigmatropic Claisen rearrangement of 62 gave the cis -2,6-disubstituted dihydropyran 63 , which upon sequential Wittig olefination with 2-(triphenylphosporanylidene)propanal and then methylenetriphenylphosphorane yielded the diene 64 .…”

Section: Reviewmentioning

confidence: 99%

Syntheses of spliceostatins and thailanstatins: a review

Donaldson¹

2020

Beilstein J. Org. Chem.

View full text Add to dashboard Cite

The spliceostatins/thailanstatins are a family of linear peptides/polyketides that inhibit pre-mRNA splicing, and as such act as potent cytotoxic compounds. These compounds generally contain 9 stereocenters spread over a common (2Z,4S)-4-acetoxy-2-butenamide fragment, an (all-cis)-2,3,5,6-tetrasubstituted tetrahydropyran fragment and a terminal oxane ring joined by a dienyl chain. Due to the impressive antitumor properties of these compounds, along with their complex structure, a number of total syntheses have been reported. This review will compare the synthetic strategies reported through the end of 2019.

show abstract

“…8 For example, Fall and co-workers recently reported a synthesis of (+)-isolaurepan employing such a strategy. 9 Commercially available tri-O-acetyl-D-glucal 1 was elaborated to ketone 2 in nine steps (Scheme 1). Treatment of ketone 2 with trimethylsilyldiazomethane and BF 3 •OEt 2 , followed by protodesilylation of the intermediate α-trimethylsilylketone, afforded 7-membered ring ether 3 in 60%…”

Section: Single-carbon Ring Expansionmentioning

confidence: 99%